Feeling threatened by Jen's very handsome new assistant, Jake, Greg tries to appear more masculine. Also, Heather and Tim pull a prank on Tyler's school, Joan secretly lets Sophia chew gum even though Heather forbids it, and John takes his new puppy on a date with Colleen and her dog, Princess.
- Colin Hanks as Greg Short
- Betsy Brandt as Heather (Short) Hughes
- Thomas Sadoski as Matthew "Matt" Short
- Zoe Lister-Jones as Jennifer "Jen" Collins-Short
- Dan Bakkeddahl as Dr. Timothy "Tim" Hughes, M.D.
- Angelique Cabral as Colleen Brandon Ortega
- Niall Cunningham as Tyler Hughes
- Holly Barrett as Samantha "Sam" Hughes
- Giselle Eisenberg as Sophia Hughes
- James Brolin as John Bertram Short
- Dianne Wiest as Dr. Joan (Pirkle) Short
- Gregg Sulkin as Jake
- Amy Hill as Principal Bundy
- River Bleu as Phoebe
- Davis Desmond as Heinz
- In the scene where Tyler's parents are meeting with school principal, a bottle of "Yes To" hand lotion appears and disappears in different shots.